CN109212905A - Hard mask composition - Google Patents
Hard mask composition Download PDFInfo
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- CN109212905A CN109212905A CN201810482175.9A CN201810482175A CN109212905A CN 109212905 A CN109212905 A CN 109212905A CN 201810482175 A CN201810482175 A CN 201810482175A CN 109212905 A CN109212905 A CN 109212905A
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
The present invention provides a kind of hard mask composition, and it includes the polymer of the repetitive unit containing specific structure and solvents.The embodiment of the present invention is capable of providing flatness, coating homogeneity, dissolubility and the excellent hard mask composition of elching resistant.
Description
Technical field
The present invention relates to hard mask compositions.
Background technique
For example, the integrated level of the works such as circuit, wiring, insulating pattern is held in the fields such as semiconductors manufacture, microelectronics
It is continuous to improve.The photo-mask process for the fine patterning of above structure object is also developed together as a result,.
In general, on etch target film painting photoresist and form photoresist layer, by exposing and showing
Shadow process and form photoresist pattern.Next, above-mentioned photoresist pattern is used as etching mask, partially remove
Above-mentioned etch target film is removed, so as to form scheduled pattern.After having carried out the image transfer to above-mentioned etch target film, on
Stating photoresist pattern can be removed by ashing (ashing) and/or removing (strip) process.
Resolution ratio caused by order to inhibit to be reflected by light in above-mentioned exposure process reduces, can be in above-mentioned etch target film
Antireflection is formed between above-mentioned photoresist layer applies (anti-refractive coating；ARC) layer.In this case,
The etching to above-mentioned ARC layer can be added, thus the consumption or etch quantity of above-mentioned photoresist layer or photoresist pattern
It can increase.In addition, the case where necessary etch quantity increases when the thickness of above-mentioned etch target film increases or forms required pattern
Under, the sufficient etching patience of required above-mentioned photoresist layer or photoresist pattern may be unable to ensure.
Therefore, in order to ensure be used to form required pattern photoresist etching patience and etching selectivity, can be with
The additional resist lower film between above-mentioned etch target film and above-mentioned photoresist layer.
Above-mentioned resist lower film is for example needed with to the sufficient elching resistant of high temperature etching process, (or etching is resistance to
Property), heat resistance, additionally need and formed for example, by spin coating process with uniform thickness.
KR published patent the 10-2010-0082844th discloses the example that resist lower film forms composition
Son.
Existing technical literature
Patent document
KR published patent the 10-2010-0082844th
Summary of the invention
Project to be solved
Project offer of the invention is capable of forming the hard mask with excellent dissolubility, coating and elching resistant
Hard mask composition.
The method to solve the problem
1. a kind of hard mask composition, it includes polymer and solvent, above-mentioned polymer includes 1 table of following chemical formula
The repetitive unit shown:
[chemical formula 1]
(in chemical formula 1, Ar1For from the aromatic functional group of carbon atom number 10~40, Ar2For from carbon original
The functional group of the aromatic compound of subnumber 6~40).
2. the hard mask composition as described in 1, the Ar of above-mentioned chemical formula 12Comprising selected from by following chemical formula Ar2- 1~
Chemical formula Ar2At least one of the group of -5 compositions:
[chemical formula Ar2-1]
[chemical formula Ar2-2]
[chemical formula Ar2-3]
[chemical formula Ar2-4]
[chemical formula Ar2-5]
3. the hard mask composition as described in 1, the polymer comprising repetitive unit represented by above-mentioned chemical formula 1 include
The condensation polymer of compound represented by the aromatic compound and following chemical formula 2 of carbon atom number 10~40:
[chemical formula 2]
(in chemical formula 2, Ar3It is derived from the functional group for the aromatic compound that carbon atom number is 6~40).
4. the hard mask composition as described in 3, the aromatic compound that above-mentioned carbon atom number is 6~40 include selected from by
At least one of hydroxyl, alkoxy and group of amido composition.
5. the hard mask composition as described in 1, above-mentioned Ar1From selected from by following chemical formula Ar1- 1~chemical formula
Ar1At least one of the group of the composition of aromatic compound represented by -4:
[chemical formula Ar1-1]
[chemical formula Ar1-2]
(in chemical formula Ar1In -2, X is-OH,-OR1Or-NR2R3, R1、R2And R3It is each independently hydrogen atom or carbon is former
The alkyl of subnumber 1~20.)
[chemical formula Ar1-3]
(in chemical formula Ar1In -3, Ar4And Ar5It is each independently phenylene or naphthylene, n1And n2It is each independently 1
Or 2 integer.)
[chemical formula Ar1-4]
(in chemical formula Ar1In -4, Y is hydrogen atom, the alkyl of carbon atom number 1~20, the alkenyl of carbon atom number 2~20, carbon
The alkynyl of atomicity 2~20 or the aryl of carbon atom number 6~25).
6. the hard mask composition as described in 1 also includes at least one in crosslinking agent, catalyst and surfactant
Kind.
Invention effect
Dissolubility, coating and etch resistant can be formed using hard mask composition involved in the embodiment of the present invention
Property the hard mask that improves simultaneously.
Hard mask involved in the embodiment of the present invention with composition may include aromatic compound with containing deriving from
Aromatic functional group connects compound condensation with the aldehyde of ether and the polymer that manufactures.Due to the revolving property of above-mentioned ether,
The flexible of above-mentioned polymer increases, so as to improve the coating uniformity or flatness of hard mask film.
In addition, the composition of hard mask involved in the embodiment of the present invention includes with the fragrance from high-carbon content
The polymer of the structure of compounds of group, so as to improve heat resistance and elching resistant.
In addition, high-resolution photo-mask process may be implemented using the hard mask formed by above-mentioned hard mask composition,
It is capable of forming the target pattern of desired fine line width.
Specific embodiment
The embodiment of the present invention provides the polymer comprising the repetitive unit containing specific structure and the hard mask of solvent is used
Composition.
The present invention by the inclusion of containing above-mentioned specific structure repetitive unit polymer, so as to provide flatness,
Coating homogeneity, dissolubility and the excellent hard mask composition of elching resistant.
Above-mentioned hard mask composition can for example be coated between photoresist layer and etch target film and form use
Make the hard mask film of resist lower film.Above-mentioned hard mask film is partially removed by photoresist pattern, so as to
Hard mask is formed, above-mentioned hard mask can be used as additional etching mask.
Above-mentioned hard mask film or hard mask for example may be used as spin-coating hardmask (Spin-On Hardmask:SOH).
In the following, being described in detail to hard mask involved in the embodiment of the present invention with composition.When in the application
Compound represented by the chemical formula used or resin are there are in the case where isomers, compound represented by the chemical formula or tree
Rouge is indicated comprising the representative chemical formula including its isomers.
Hard mask involved in the embodiment of the present invention includes to contain repetition list represented by following chemical formula 1 with composition
The polymer and solvent of member can also include the additional preparation such as crosslinking agent, catalyst, surfactant.
<polymer containing repetitive unit represented by chemical formula 1>
In the hard mask composition involved in the embodiment of the present invention, this field can be used without particular limitation
In well known carbon system SOH composition in include macromolecule or resinous substances.
According to illustrative embodiment, in order to ensure the heat resistance of hard mask film, at least one aromatic compound gathers
Closing object (for example, condensation polymer) may be used as the basic substance of above-mentioned hard mask composition.
In embodiment, above-mentioned polymer may include repetitive unit represented by chemical formula 1.
[chemical formula 1]
Above-mentioned in chemical formula 1, Ar1For from the aromatic functional group of carbon atom number 10~40, Ar2For source
In the functional group of the aromatic compound of carbon atom number 6~40.
The present invention is by the inclusion of the polymer containing repetitive unit represented by above-mentioned chemical formula 1, so as to have simultaneously
There are excellent flatness, coating homogeneity, dissolubility and elching resistant.
Specifically, by including ether in the repetitive unit represented by above-mentioned chemical formula 1, thus because of the rotation of ether
Characteristic and include that its compound or the flexible of polymer increase, can be improved the flatness of hard mask film, in addition, due to poly-
It closes to may include aryloxy group in object and carry out replacement and can generate the hydrogen atom or hydroxyl of the stronger gravitation such as hydrogen bond, therefore composition
Viscosity reduce and can be improved dissolubility.
In addition, the polymer comprising repetitive unit represented by above-mentioned chemical formula 1 includes aromatic compound or polycyclic virtue
The condensation product of fragrant compounds of group, so that the carbon content (C-contents:C%) of unit formula can increase.Thereby, it is possible to improve
Etching patience or elching resistant of the hard mask comprising above-mentioned polymer to etching gas or etching solution.
Above-mentioned in chemical formula 1, Ar1It can be for from the function of the aromatic compound of carbon atom number 10~40
Group, preferably can be for from the functional group of the aromatic compound of carbon atom number 10~25, Ar2It can be for from carbon atom
The functional group of the aromatic compound of number 6~40, preferably can be for from the official of the aromatic compound of carbon atom number 6~25
It can group.
If deriving from the functional group A r of above-mentioned aromatic compound1And Ar2Carbon atom number be more than 40, then due to polymerization
The solubility of object excessively reduces, thus the flatness of hard mask, coating uniformity may be decreased.If Ar1Carbon atom number be
10 hereinafter, can then worry the reduction due to carbon content and elching resistant reduction.
In a part of the embodiment, the Ar of above-mentioned chemical formula 12It may include selected from by following chemical formula Ar2- 1~chemical formula
Ar2At least one of the group of -5 compositions.
[chemical formula Ar2-1]
[chemical formula Ar2-2]
[chemical formula Ar2-3]
[chemical formula Ar2-4]
[chemical formula Ar2-5]
Include above-mentioned chemical formula Ar2- 1~chemical formula Ar2Carbon of the polymer of functional group represented by -5 due to unit formula
Content is high, thus from the aspect of elching resistant and it is preferred that.In addition, above-mentioned chemical formula Ar2- 1~chemical formula Ar2Represented by -5
Functional group forms aryloxy group due to connecting with oxygen atom, is able to maintain that proper viscosity and further increases dissolubility.
In a part of the embodiment, the polymer comprising repetitive unit represented by above-mentioned chemical formula 1 can wrap carbon containing original
The condensation polymer of compound represented by the aromatic compound and following chemical formula 2 of subnumber 10~40.Above-mentioned polymer passes through packet
Containing containing the condensation polymer for connecting with aldehyde represented by the following chemical formula 2 of ether compound from aromatic functional group, from
And the raising of coating uniformity and aryloxy group institute band brought by the revolving property of ether can be assigned to hard mask composition
The dissolubility come improves.
[chemical formula 2]
In above-mentioned chemical formula 2, Ar3For from the functional group of the aromatic compound of carbon atom number 6~40.
For example, compound represented by above-mentioned chemical formula 2 can be illustrated by following chemical formula 2-1~chemical formula 2-5.
[chemical formula 2-1]
[chemical formula 2-2]
[chemical formula 2-3]
[chemical formula 2-4]
[chemical formula 2-5]
In a part of the embodiment, the above-mentioned carbon atom number of condensation polymer is formed with compound represented by above-mentioned chemical formula 2
10~40 aromatic compound may include hydroxyl, alkoxy and/or amido, it is possible thereby to be easily manufactured and above-mentioned aldehyde
Connect the condensation polymer of compound.
In one embodiment, the Ar of above-mentioned chemical formula 11It can be from selected from by following chemical formula Ar1- 1~chemical formula
Ar1At least one of the group of the composition of aromatic compound represented by -4.
[chemical formula Ar1-1]
[chemical formula Ar1-2]
In above-mentioned chemical formula Ar1In -2, X is-OH,-OR1Or-NR2R3, R1、R2And R3It is each independently hydrogen atom or carbon
The alkyl of atomicity 1~20.
[chemical formula Ar1-3]
In above-mentioned chemical formula Ar1In -3, Ar4And Ar5It is each independently phenylene or naphthylene, n1And n2Each independently
For an integer of 1 or 2.
[chemical formula Ar1-4]
In above-mentioned chemical formula Ar1In -4, Y be hydrogen atom, the alkyl of carbon atom number 1~20, carbon atom number 2~20 alkene
The aryl of base, the alkynyl of carbon atom number 2~20 or carbon atom number 6~25.
In an embodiment of the present invention, the content of the polymer comprising repetitive unit represented by above-mentioned chemical formula 1 does not have
Especially limitation, such as can be about 5~30 weight % in hard mask composition total weight, can be with when meeting the above range
Optimal strange land shows effect of the invention.
In one embodiment, the weight average molecular weight of the polymer comprising repetitive unit represented by above-mentioned chemical formula 1 is for example
It can ensure suitable dissolubility, elching resistant and flat simultaneously within the above range in about 1500~10000 ranges
Property.
In one embodiment, the polymer comprising repetitive unit represented by above-mentioned chemical formula 1 polydispersity index (PDI,
Polydispersity index) [weight average molecular weight (Mw)/number-average molecular weight (Mn)] can be about 1.5~6.0, and it preferably can be with
It is about 1.5~3.0.It can ensure suitable dissolubility, elching resistant and flatness simultaneously within the above range.
When above-mentioned polydispersity index [weight average molecular weight (Mw)/number-average molecular weight (Mn)] includes within the above range, by wrapping
Compound bring effect containing repetitive unit represented by above-mentioned chemical formula 1 is more excellent, therefore preferably.
<solvent>
Hard mask solvent used in composition involved in the embodiment of the present invention is not particularly limited, and may include
There is sufficient deliquescent organic solvent to the polymer of above-mentioned aromatic compound.For example, above-mentioned solvent may include third
Glycol monomethylether acetate (propylene glycol monomethyl etheracetate；PGMEA), propylene glycol monomethyl ether
(propylene glycol monomethyl ether；PGME), cyclohexanone, ethyl lactate, gamma-butyrolacton (γ-
butyrolactone；GBL), acetylacetone,2,4-pentanedione (acetyl acetone) etc..
The content of above-mentioned solvent is not particularly limited, content can in addition to above-mentioned aromatic compound polymer and
Surplus other than aftermentioned additional preparation.For example, above-mentioned solvent can include 50~90 in hard mask composition total weight
Weight % can effectively show above-mentioned effect of the invention when meeting the above range.
<additional preparation>
Selectively, hard mask composition involved in the embodiment of the present invention can further include crosslinking agent, urge
The addition preparation of agent, surfactant etc.
The repetitive unit of the polymer of above-mentioned aromatic compound can be crosslinked by above-mentioned crosslinking agent, for example, can with it is upper
The hydroxyl for stating polymer is reacted.Using above-mentioned crosslinking agent, the curing characteristics of hard mask composition can be further enhanced.
As the example of above-mentioned crosslinking agent, melamine, amino resins, glycoluril compounds or diepoxides can be enumerated
Deng.
For above-mentioned crosslinking agent, if enumerating specific example, the amino resins of etherificate, such as methyl may include
Change or butylated melamine (as specific example, N- methoxy-melamine or N- butoxymethyl-trimerization
Cyanamide) and methylation or butylated urea (urea) resin (as specific example, Cymel U-65 resin or UFR 80
Resin), glycolurii derivative (as specific example having Powderlink 1174 referring to chemical formula 3), represented by chemical formula 4
Bis- (methylol) paracresol compounds etc..In addition, the compound of bis-epoxy system and following chemistry represented by following chemical formula 5
The compound of melamine series represented by formula 6 also can be used as crosslinking agent use.
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
As above-mentioned catalyst, acid catalyst or basic catalyst can be used.
The acid catalyst of thermal activation can be used in above-mentioned acid catalyst.As the example of acid catalyst, can be used to first
The organic acid of benzene sulfonic acid etc.As above-mentioned acid catalyst, thermal acid generator (thermal acid can also be used
Generator:TAG) the compound of system.As the example of above-mentioned thermal acid generator series catalysts, p-methyl benzenesulfonic acid pyridine can be enumeratedSalt (pyridinium p-toluene sulfonate), 2,4,4,6- tetrabromo cyclohexadienone, benzoin tosylate,
2- nitrobenzyl tosylat, Arrcostab of organic sulfonic acid etc..
As above-mentioned basic catalyst, can be used selected from NH4OH or NR4Ammonium hydroxide represented by OH (R is alkyl)
In any one.
In the case where comprising above-mentioned crosslinking agent, relative to 100 parts by weight of polymer of above-mentioned aromatic compound, crosslinking agent
Content can be about 1~30 parts by weight, preferably can be about 5~20 parts by weight, more preferably can be about 5~10 parts by weight.
In the case where comprising above-mentioned catalyst, relative to 100 parts by weight of polymer of above-mentioned aromatic compound, the content of catalyst can
Think about 0.001~5 parts by weight, preferably can be about 0.1~2 parts by weight, more preferably can be about 0.1~1 parts by weight.
It, can be in the polymerization for not making above-mentioned aromatic compound in the content range of above-mentioned crosslinking agent and above-mentioned catalyst
In the case that elching resistant, heat resistance, the flatness of object deteriorate, suitable crosslinking feature is obtained.
In order to improve surface characteristic, the cementability of hard mask, hard mask composition involved in the embodiment of the present invention
It can also include surfactant.As surfactant, alkylbenzene sulfonate, alkyl pyridine can be usedSalt, poly- second two
Alcohols, quaternary ammonium salt etc., but not limited thereto.Relative to 100 parts by weight of polymer of above-mentioned aromatic compound, above-mentioned surface is living
The content of property agent for example can be about 0.1~10 parts by weight.
Hereinafter, the experimental example including specific embodiment and comparative example is provided in order to facilitate understanding of the invention,
But this only illustrates the present invention, is not intended to limit appended claims range, those skilled in the art understand in model of the invention
Can carry out numerous variations and modification within the scope of farmland and technical idea to embodiment, certainly such change and modification also belong to
Attached scope of the claims.
Embodiment and comparative example
Manufacture the hard mask composition of the composition recorded and content (weight %) in following table 1.In embodiment and compare
In example, when forming polymer (A), as acid catalyst, (it is relative to aromatic compound using p-methyl benzenesulfonic acid
5mol%).
[table 1]
A-1: willThe polymer for carrying out polycondensation and generating
(weight average molecular weight: 5100, PDI:2.3)
A-2: willIt carries out polycondensation and generates poly-
Close object (weight average molecular weight: 5500, PDI:2.1)
A-3: willIt carries out polycondensation and generates
Polymer (weight average molecular weight: 5600, PDI:2.7)
A-4: willPolymer (the Weight-average molecular for carrying out polycondensation and generating
Amount: 4800, PDI:1.9)
A-5: willPolymer (the weight for carrying out polycondensation and generating
Average molecular weight: 3500, PDI:1.8)
A-6: willThe polymer for carrying out polycondensation and generating
(weight average molecular weight: 2300, PDI:2.1)
A-7: willThe polymer for carrying out polycondensation and generating
(weight average molecular weight: 1900, PDI:2.5)
A ' -1: willCarry out polycondensation and generate polymer (weight average molecular weight:
3800, PDI:2.5)
A ' -2: willThe polymer for carrying out polycondensation and generating (is divided equally again
Son amount: 2800, PDI:2.1)
A ' -3: willThe polymer for carrying out polycondensation and generating (is divided equally again
Son amount: 1900, PDI:2.5)
A ' -4: willCarry out polycondensation and generate polymer (weight average molecular weight:
2300, PDI:3.1)
A ' -5: willThe polymer for carrying out polycondensation and generating is (heavy equal
Molecular weight: 5900, PDI:2.3)
B-1:PGMEA
C-1:N- methoxy-melamine resin
D-1: p-methyl benzenesulfonic acid pyridineSalt
E-1: triethylene glycol
Experimental example
It evaluated by aftermentioned evaluation method by the dissolubility of the composition of table 1 hard mask layer formed or hard mask, put down
Smooth property and elching resistant.Evaluation result is shown in following table 2.
(1) dissolubility
By the composition of embodiment and comparative example after 50 DEG C are stirred 1 hour, dissolubility is measured as follows: 1) confirmation heating shape
2) dissolved state of polymer under state (50 DEG C) after being cooled to room temperature, confirms the polymer under normal temperature state (25 DEG C) at once
Dissolved state, further stir 6 hours in room temperature, 3) reaffirm the molten of polymer under room temperature state (25 DEG C)
Solution state.
<dissolution sex determination>
◎: undissolved polymer is not confirmed under room temperature state visually.
Zero: although not confirming undissolved polymer visually under normal temperature state, the meat under room temperature state
Eye confirms a small amount of undissolved polymer.
△: although not confirming undissolved polymer visually in a heated state, naked eyes are true under normal temperature state
Recognize undissolved polymer.
×: a small amount of undissolved polymer is visually confirmed in a heated state.
(2) flatness is evaluated
It is including the SiO of the groove of 10 μm of width, 0.50 μm of depth by the composition of embodiment and comparative example2Wafer substrate
On be coated and dry and form hard mask film, utilize scanning electron microscope (SEM) observation trench portions and non-groove portion
/ thickness difference, to evaluate flatness.
<flat sex determination>
◎: thickness difference is less than 150nm
Zero: thickness difference is 150 more than and less than 175nm
△: thickness difference is 175 more than and less than 200nm
×: thickness difference is greater than 200nm
(3) elching resistant is evaluated
Composition according to examples and comparative examples is coated on silicon wafer with method of spin coating respectively, is carried out at 200 DEG C
Baking in 60 seconds and formed with a thickness ofFilm.ArF photoresist is coated on each film of formation, at 110 DEG C
After baking 60 seconds, after being exposed respectively using the exposure sources of ASML (XT:1450G, NA0.93) company, TMAH is used
(2.38wt% aqueous solution) develops respectively, obtains the lines and space (line and space) pattern of 60nm.
The patterned test piece of acquisition is further solidified 60 seconds at 110 DEG C, test piece is used into CHF3/CF4Mixed gas point
Dry-etching that carry out be 20 seconds observes section with FE-SEM respectively, measures etching speed, determines to the resistance to of halogen plasma
Etching.
<elching resistant judgement>
◎: etching speed is less than
Zero: etching speed isMore than and less than
△: etching speed isMore than and less than
×: etching speed isMore than
[table 2]
| It distinguishes | Dissolubility | Flatness | Elching resistant |
| Embodiment 1 | ◎ | ◎ | ◎ |
| Embodiment 2 | ◎ | ◎ | ○ |
| Embodiment 3 | ◎ | ◎ | ◎ |
| Embodiment 4 | ◎ | ◎ | ○ |
| Embodiment 5 | ◎ | ◎ | ○ |
| Embodiment 6 | ○ | ○ | ◎ |
| Embodiment 7 | ○ | ○ | ◎ |
| Embodiment 8 | ◎ | ○ | ○ |
| Embodiment 9 | ○ | ○ | ◎ |
| Embodiment 10 | ◎ | ◎ | ◎ |
| Embodiment 11 | ◎ | ◎ | ◎ |
| Comparative example 1 | △ | ○ | ○ |
| Comparative example 2 | △ | △ | ○ |
| Comparative example 3 | × | × | ◎ |
| Comparative example 4 | × | × | ◎ |
| Comparative example 5 | ○ | ○ | × |
Referring to table 2, the reality of the polymer comprising repetitive unit represented by above-mentioned chemical formula 1 disclosed herein is used
In the case where applying example, compared with comparative example, dissolubility, flatness and elching resistant are excellent.
In the case where embodiment 10, elching resistant evaluation result is ◎, is marked as being identical with the situation of embodiment 1, but
Be by being used together with crosslinking agent and catalyst, with embodiment 1 the case where compared with, since the degree of cross linking improves, thus etch resistant
Property further increases.
In the case where embodiment 8, since the content of polymer (A) is few, so when in the presence of forming hard mask layer or hard mask
It is difficult to the shortcomings that obtaining desired thickness.
In the case where embodiment 9, since the content of polymer (A) is more, so compared with other embodiments, dissolubility peace
How much smooth property effect reduces, and how much coating is deteriorated.
Claims (6)
1. a kind of hard mask composition, it includes polymer and solvent, the polymer includes represented by following chemical formula 1
Repetitive unit:
Chemical formula 1
In chemical formula 1, Ar1For from the aromatic functional group of carbon atom number 10~40, Ar2For from carbon atom number 6
The functional group of~40 aromatic compound.
2. hard mask composition according to claim 1, the Ar of the chemical formula 12Comprising selected from by following chemical formula
Ar2- 1~chemical formula Ar2At least one of the group of -5 compositions:
Chemical formula Ar2-1
Chemical formula Ar2-2
Chemical formula Ar2-3
Chemical formula Ar2-4
Chemical formula Ar2-5
3. hard mask composition according to claim 1, the polymerization comprising repetitive unit represented by the chemical formula 1
Object includes the condensation polymer of the aromatic compound and compound represented by following chemical formula 2 of carbon atom number 10~40:
Chemical formula 2
In chemical formula 2, Ar3It is derived from the functional group of the aromatic compound of carbon atom number 6~40.
4. hard mask composition according to claim 3, the aromatic compound of the carbon atom number 6~40 includes choosing
At least one of free hydroxyl, alkoxy and group of amido composition.
5. hard mask composition according to claim 1, the Ar1From selected from by following chemical formula Ar1- 1~change
Formula Ar1At least one of the group of the composition of aromatic compound represented by -4:
Chemical formula Ar1-1
Chemical formula Ar1-2
In chemical formula Ar1In -2, X is-OH,-OR1Or-NR2R3, R1、R2And R3Be each independently hydrogen atom or carbon atom number 1~
20 alkyl,
Chemical formula Ar1-3
In chemical formula Ar1In -3, Ar4And Ar5It is each independently phenylene or naphthylene, n1And n2It is each independently 1 or 2
Integer,
Chemical formula Ar1-4
In chemical formula Ar1In -4, Y is hydrogen atom, the alkyl of carbon atom number 1~20, the alkenyl of carbon atom number 2~20, carbon atom number
2~20 alkynyl or the aryl of carbon atom number 6~25.
6. hard mask composition according to claim 1 also includes in crosslinking agent, catalyst and surfactant
It is at least one.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020170083374A KR102383692B1 (en) | 2017-06-30 | 2017-06-30 | Composition for hard mask |
| KR10-2017-0083374 | 2017-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109212905A true CN109212905A (en) | 2019-01-15 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111290216A (en) * | 2020-02-12 | 2020-06-16 | 厦门恒坤新材料科技股份有限公司 | Hardmask composition, hardmask and method of forming pattern |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3307940A (en) * | 1959-05-30 | 1967-03-07 | Azoplate Corp | Electrophotographic process employing photoconductive polymers |
| CN101185030A (en) * | 2005-05-27 | 2008-05-21 | 第一毛织株式会社 | Antireflective hardmask composition and methods for using same |
| CN101802713A (en) * | 2007-10-01 | 2010-08-11 | 日产化学工业株式会社 | Composition for forming resist underlayer film, process for producing semiconductor device with the same, and additive for composition for forming resist underlayer film |
| CN102803324A (en) * | 2009-06-19 | 2012-11-28 | 日产化学工业株式会社 | Carbazole Novolak Resin |
| CN103229104A (en) * | 2010-12-09 | 2013-07-31 | 日产化学工业株式会社 | Composition for forming resist underlayer film containing hydroxyl group-containing carbazole novolac resin |
| JP2014029435A (en) * | 2012-07-31 | 2014-02-13 | Nissan Chem Ind Ltd | Resist underlay film-forming composition for lithography including carbonyl group-containing carbazole novolac |
| US20140363768A1 (en) * | 2010-09-10 | 2014-12-11 | Shin-Etsu Chemical Co., Ltd. | Naphthalene derivative, resist bottom layer material, and patterning process |
| CN105143979A (en) * | 2013-04-17 | 2015-12-09 | 日产化学工业株式会社 | Composition for forming resist underlayer film |
| CN105555888A (en) * | 2013-09-19 | 2016-05-04 | 日产化学工业株式会社 | Composition for forming underlayer film of self-assembling film including aliphatic polycyclic structure |
| KR20170034488A (en) * | 2015-09-21 | 2017-03-29 | (주)디엔에프 | New polymer and compositions for hardmask containing it |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100908601B1 (en) * | 2007-06-05 | 2009-07-21 | 제일모직주식회사 | Anti-reflective hard mask composition and patterning method of substrate material using same |
| KR101400183B1 (en) * | 2010-07-06 | 2014-05-30 | 제일모직 주식회사 | Aromatic ring-containing compound for resist underlayer, resist underlayer composition including same, and method of patterning device using same |
| KR101655394B1 (en) * | 2013-04-25 | 2016-09-07 | 제일모직 주식회사 | Resist underlayer composition, method of forming patterns and semiconductor integrated circuit device including the patterns |
| KR102296794B1 (en) * | 2016-07-28 | 2021-08-31 | 삼성에스디아이 주식회사 | Polymer, organic layer composition, and method of forming patterns |
-
2017
- 2017-06-30 KR KR1020170083374A patent/KR102383692B1/en active IP Right Grant
-
2018
- 2018-05-18 CN CN201810482175.9A patent/CN109212905B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3307940A (en) * | 1959-05-30 | 1967-03-07 | Azoplate Corp | Electrophotographic process employing photoconductive polymers |
| CN101185030A (en) * | 2005-05-27 | 2008-05-21 | 第一毛织株式会社 | Antireflective hardmask composition and methods for using same |
| CN101802713A (en) * | 2007-10-01 | 2010-08-11 | 日产化学工业株式会社 | Composition for forming resist underlayer film, process for producing semiconductor device with the same, and additive for composition for forming resist underlayer film |
| CN102803324A (en) * | 2009-06-19 | 2012-11-28 | 日产化学工业株式会社 | Carbazole Novolak Resin |
| US20140363768A1 (en) * | 2010-09-10 | 2014-12-11 | Shin-Etsu Chemical Co., Ltd. | Naphthalene derivative, resist bottom layer material, and patterning process |
| CN103229104A (en) * | 2010-12-09 | 2013-07-31 | 日产化学工业株式会社 | Composition for forming resist underlayer film containing hydroxyl group-containing carbazole novolac resin |
| JP2014029435A (en) * | 2012-07-31 | 2014-02-13 | Nissan Chem Ind Ltd | Resist underlay film-forming composition for lithography including carbonyl group-containing carbazole novolac |
| CN105143979A (en) * | 2013-04-17 | 2015-12-09 | 日产化学工业株式会社 | Composition for forming resist underlayer film |
| CN105555888A (en) * | 2013-09-19 | 2016-05-04 | 日产化学工业株式会社 | Composition for forming underlayer film of self-assembling film including aliphatic polycyclic structure |
| KR20170034488A (en) * | 2015-09-21 | 2017-03-29 | (주)디엔에프 | New polymer and compositions for hardmask containing it |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111290216A (en) * | 2020-02-12 | 2020-06-16 | 厦门恒坤新材料科技股份有限公司 | Hardmask composition, hardmask and method of forming pattern |
| CN111290216B (en) * | 2020-02-12 | 2022-05-20 | 厦门恒坤新材料科技股份有限公司 | Hard mask composition, hard mask and method for forming pattern |
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| Publication number | Publication date |
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| KR102383692B1 (en) | 2022-04-05 |
| KR20190002988A (en) | 2019-01-09 |
| CN109212905B (en) | 2021-10-26 |
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